In the long-standing debate on the role of bottom-up and top-down mechanisms for visual attention, the additional importance of associative learning has recently been emphasized and investigated more thoroughly. In two experiments we examined to which extent top-down mechanisms interact with an observer's individual learning experience in guiding attention. To induce associative learning, a categorization learning task was combined with an additional singleton search task in the same experimental blocks. A high degree of top-down control was enabled by presentation of advance task cues, or by complete predictability of a fixed continuous task sequence. Event-related potentials and behavioral performance measures served as indicator of attention deployment. Results showed that attention deployment during search was biased by the individual experience in the learning task: When a distractor was defined in the same dimension that observers had experienced as being predictive in the categorization learning task, it impaired visual search more strongly than when the dimension was unpredictive in the learning task. Event-related potentials indicated that the magnitude of this effect was modulated by the nature of provided top-down control. Yet, even with the highest degree of top-down control, learning effects were not entirely overruled. These results indicate that associative learning experience considerably shapes attention deployment and may significantly oppose or even undermine preparatory top-down efforts.